Iron cyclopentadienone complexes: Discovery, properties, and catalytic reactivity

Angewandte Chemie - International Edition

Volumn 53, Issue 16, 2014, Pages 4044-4055

  Quintard, Adrien ^a   Rodriguez, Jean ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

bifunctional catalysis; dual catalysis; hydrogenation; iron catalysis; synthetic methods

Indexed keywords

CATALYSIS; CHELATION; ENANTIOSELECTIVITY; HYDROGENATION; IRON; LIGANDS; REDOX REACTIONS;

BIFUNCTIONAL CATALYSIS; CATALYTIC REACTIVITY; DUAL CATALYSIS; ENANTIOSELECTIVE REACTIONS; IRON CATALYSIS; NON-INNOCENT LIGANDS; ORGANIC CHEMISTRY; SYNTHETIC METHODS;

SYNTHESIS (CHEMICAL);

EID: 84898623394     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201310788     Document Type: Review

References (110)

1. D. J. Ager, A. H. M. de Vries, J. G. de Vries, Chem. Soc. Rev. 2012, 41, 3340
2. H. Shimizu, I. Nagasaki, K. Matsumara, N. Sayo, T. Saito, Acc. Chem. Res. 2007, 40, 1385
3. N. B. Johnson, I. C. Lennon, P. H. Moran, J. A. Ramsden, Acc. Chem. Res. 2007, 40, 1291.
4. R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40
5. Angew. Chem. Int. Ed. 2001, 40, 40
6. T. Ikariya, K. Murata, R. Noyori, Org. Biomol. Chem. 2006, 4, 393
7. V. Lyaskovskyy, B. de Bruin, ACS Catal. 2012, 2, 270
8. O. R. Luca, R. H. Crabtree, Chem. Soc. Rev. 2013, 42, 1440
9. O. Eisenstein, R. H. Crabtree, New J. Chem. 2013, 37, 21.
10. Y. Blum, D. Czarkie, Y. Rahamim, Y. Shvo, Organometallics 1985, 4, 1459
11. Y. Shvo, D. Czierkie, Y. Rahamin, D. F. Ghodosh, J. Am. Chem. Soc. 1986, 108, 7400. For Reviews on the Shvo catalyst
12. R. Prabhakaran, Synlett 2004, 2048
13. R. Karvembu, R. Prabhakaran, K. Natarajan, Coord. Chem. Rev. 2005, 249, 911
14. B. L. Conley, M. K. Pennington-Boggio, E. Boz, T. J. Williams, Chem. Rev. 2010, 110, 2294.
15. S. Gaillard, J.-L. Renaud, ChemSusChem 2008, 1, 505
16. H. Nakazawa, M. Itazaki, Top. Organomet. Chem. 2011, 33, 27
17. K. Junge, K. Schröder, M. Beller, Chem. Commun. 2011, 47, 4849
18. J. Yang, X. Liu, D.-L. Meng, H.-Y. Chen, Z.-H. Zong, T.-T. Feng, K. Sun, Adv. Synth. Catal. 2012, 354, 328.
19. J. C. Fontecilla-Camps, A. Volbeda, C. Cavazza, Y. Nicolet, Chem. Rev. 2007, 107, 4273
20. S. Shima, O. Pilak, S. Vogt, M. Schick, M. S. Stagni, W. Meyer-Klaucke, E. Warkentin, R. K. Thauer, U. Elmer, Science 2008, 321, 572.
21. Y. Shvo, I. Goldberg, D. Czerkie, D. Reshef, Z. Stein, Organometallics 1997, 16, 133
22. N. Menashe, E. Salant, Y. Shvo, J. Organomet. Chem. 1996, 514, 97
23. J. S. M. Samec, J.-E. Bäckvall, Chem. Eur. J. 2002, 8, 2955
24. Y. Yuki, K. Takahashi, Y. Tanaka, K. Nozaki, J. Am. Chem. Soc. 2013, 135, 17393.
25. M. L. S. Almeida, M. Beller, G.-Z. Wang, J.-E. Bäckvall, Chem. Eur. J. 1996, 2, 1533
26. M. L. S. Almeida, P. Koovsk, J.-E. Bäckvall, J. Org. Chem. 1996, 61, 6587
27. G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin, J.-E. Bäckvall, J. Org. Chem. 2002, 67, 1657
28. A. H. Éll, J. S. M. Samec, C. Brasse, J.-E. Bäckvall, Chem. Commun. 2002, 1144
29. E. Haak, Synlett 2006, 1847
30. E. Haak, Eur. J. Org. Chem. 2007, 2815
31. S. Muthaiah, S. H. Hong, Adv. Synth. Catal. 2012, 354, 3045.
32. D. Hollmann, S. Bähn, A. Tillack, M. Beller, Angew. Chem. 2007, 119, 8440
33. Angew. Chem. Int. Ed. 2007, 46, 8291
34. L. Neubert, D. Michalik, S. Bähn, S. Imm, H. Neumann, J. Atzrodt, V. Derdau, W. Holla, M. Beller, J. Am. Chem. Soc. 2012, 134, 12239.
35. A. L. E. Larsson, B. A. Perssonn, J. E. Bäckvall, Angew. Chem. 1997, 109, 1256
36. Angew. Chem. Int. Ed. Engl. 1997, 36, 1211
37. B. Martín-Matute, J. E. Backvall, Curr. Opin. Chem. Biol. 2007, 11, 226.
38. A. Jonek, S. Berger, E. Haak, Chem. Eur. J. 2012, 18, 15504
39. N. Thies, C. G. Hrib, E. Haak, Chem. Eur. J. 2012, 18, 6302
40. N. Thies, M. Gerlach, E. Haak, Eur. J. Org. Chem. 2013, 7354.
41. W. Reppe, H. Vetter, Liebigs Ann. Chem. 1953, 582, 133.
42. I. Wender, R. A. Friedel, R. Markby, H. W. Sternberg, J. Am. Chem. Soc. 1955, 77, 4946
43. I. Wender, R. A. Friedel, R. Markby, H. W. Sternberg, J. Am. Chem. Soc. 1956, 78, 3621
44. G. N. Schrauzer, Chem. Ind. 1958, 1403
45. E. Weiss, R. Merenyi, W. Hubel, Chem. Ind. 1960, 407.
46. G. N. Schrauzer, J. Am. Chem. Soc. 1959, 81, 5307.
47. J. L. Boston, D. W. A. Sharp, G. Wilkinson, J. Chem. Soc. 1962, 3488
48. C. G. Krespan, J. Org. Chem. 1975, 40, 261
49. R. S. Dickson, C. Mok, G. Connor, Aust. J. Chem. 1977, 30, 2143
50. R. J. Kazlauskas, M. S. Wrighton, Organometallics 1982, 1, 602
51. D. Fornals, M. A. Pericàs, F. Serratosa, J. Vinaixa, M. Font-Altaba, X. Solans, J. Chem. Soc. Perkin Trans. 1 1987, 2749
52. A. J. Pearson, J. B. Kim, Org. Lett. 2002, 4, 2837
53. J. D. Rainier, J. E. Imbriglio, J. Org. Chem. 2000, 65, 7272.
54. H.-J. Knölker, J. Heber, C. H. Mahler, Synlett 1992, 1002
55. H.-J. Knölker, J. Heber, Synlett 1993, 924
56. H.-J. Knölker, E. Baum, R. Klauss, Tetrahedron Lett. 1995, 36, 7647.
57. A. J. Pearson, R. A. Dubbert, J. Chem. Soc. Chem. Commun. 1991, 202
58. A. J. Pearson, R. J. Shively, Jr., R. A. Dubbert, Organometallics 1992, 11, 4096
59. A. J. Pearson, R. J. Shively, Jr., Organometallics 1994, 13, 578
60. A. J. Pearson, A. Perosa, Organometallics 1995, 14, 5178
61. A. J. Pearson, X. Yao, Synlett 1997, 1281.
62. H.-J. Knölker, H. Goesmann, R. Klauss, Angew. Chem. 1999, 111, 727
63. Angew. Chem. Int. Ed. 1999, 38, 702.
64. H.-J. Knölker, E. Baum, H. Goesmann, R. Klauss, Angew. Chem. 1999, 111, 2196
65. Angew. Chem. Int. Ed. 1999, 38, 2064.
66. For a related cyclopentadienyl iron hydride complex, see:, T. A. Shackleton, S. C. Mackie, S. B. Fergusson, L. J. Johnston, M. C. Baird, Organometallics 1990, 9, 2248.
67. C. P. Casey, H. Guan, J. Am. Chem. Soc. 2007, 129, 5816; For an Highlight on this discovery
68. R. M. Bullock, Angew. Chem. 2007, 119, 7504
69. Angew. Chem. Int. Ed. 2007, 46, 7360.
70. A. Pagnoux-Ozherelyeva, N. Pannetier, M. D. Mbaye, S. Gaillard, J.-L. Renaud, Angew. Chem. 2012, 124, 5060
71. Angew. Chem. Int. Ed. 2012, 51, 4976. For a recent Full Paper on this work
72. S. Moulin, H. Dentel, A. Pagnoux-Ozherelyeva, S. Gaillard, A. Poater, L. Cavallo, J.-F. Lohier, J.-L. Renaud, Chem. Eur. J. 2013, DOI:.
73. D. S. Mérel, M. Elie, J.-F. Lohier, S. Gaillard, J.-L. Renaud, ChemCatChem 2013, 5, 2939.
74. S. Fleischer, S. S. Zhou, K. Junge, M. Beller, Angew. Chem. 2013, 125, 5224
75. Angew. Chem. Int. Ed. 2013, 52, 5120.
76. A. Tlili, J. Schranck, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 15935.
77. T. N. Plank, J. L. Drake, D. K. Kim, T. W. Funk, Adv. Synth. Catal. 2012, 354, 597. For a similar activation by acetonitrile complex formation see Ref. [17].
78. M. K. Thorson, K. L. Klinkel, J. Wang, T. J. Williams, Eur. J. Inorg. Chem. 2009, 295.
79. M. G. Coleman, A. N. Brown, B. A. Bolton, H. Guan, Adv. Synth. Catal. 2010, 352, 967.
80. S. A. Moyer, T. Funk, Tetrahedron Lett. 2010, 51, 5430.
81. T. C. Johnson, G. J. Clarkson, M. Wills, Organometallics 2011, 30, 1859.
82. For a recent Palladium-catalyzed borrowing hydrogen oxidation of thiols, see:, A. Corma, J. Navas, T. Rodenas, M. J. Sabater, Chem. Eur. J. 2013, 19, 17464.
83. M. Darwish, M. Wills, Catal. Sci. Technol. 2012, 2, 243
84. K. Gopalaiah, Chem. Rev. 2013, 113, 3248. For a recent report of an efficient chiral iron catalyst see
85. W. Zuo, A. J. Lough, Y. F. Li, R. H. Morris, Science 2013, 342, 1080.
86. A. Berkessel, S. Reichau, A. von der Höh, N. Leconte, J.-M. Neudörfl, Organometallics 2011, 30, 3880.
87. J. P. Hopewell, J. E. D. Martins, T. C. Johnson, J. Godfrey, M. Wills, Org. Biomol. Chem. 2012, 10, 134.
88. Y. Yamamoto, K. Yamashita, M. Nakamura, Organometallics 2010, 29, 18472.
89. C. P. Casey, H. Guan, Organometallics 2012, 31, 2631.
90. C. P. Casey, H. Guan, J. Am. Chem. Soc. 2009, 131, 2499.
91. H. Zhang, D. Chen, Y. Zhang, G. Zhang, J. Liu, Dalton Trans. 2010, 39, 1972
92. A. Von der Hör, A. Berkessel, ChemCatChem 2011, 3, 861
93. X. Lu, Y. Zhang, P. Yun, M. Zhang, T. Li, Org. Biomol. Chem. 2013, 11, 5264.
94. C. P. Casey, S. W. Singer, D. R. Powell, R. K. Hayashi, M. Kavana, J. Am. Chem. Soc. 2001, 123, 1090
95. J. B. Johnson, J. E. Bäckvall, J. Org. Chem. 2003, 68, 7681
96. C. P. Casey, G. A. Bikzhanova, Q. Cui, I. A. Guzei, J. Am. Chem. Soc. 2005, 127, 14062
97. A. Comas-Vives, G. Ujaque, A. Lledõs, Organometallics 2007, 26, 4135; and Ref. [3c]. In an inner-sphere mechanism the substrate coordinates to the metal center prior to reacting, whereas in an outer-sphere mechanism the substrate reacts outside of the metal coordination sphere.
98. A. E. Allen, D. W. C. MacMillan, Chem. Sci. 2012, 3, 633
99. C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999-3025
100. Z. Du, Z. Shao, Chem. Soc. Rev. 2013, 42, 1337.
101. S. Zhou, S. Fleischer, K. Junge, M. Beller, Angew. Chem. 2011, 123, 5226
102. Angew. Chem. Int. Ed. 2011, 50, 5120.
103. S. Fleischer, S. Werkmeister, S. Zhou, K. Junge, M. Beller, Chem. Eur. J. 2012, 18, 9005.
104. S. Fleischer, S. Zhou, S. Wermeister, K. Junge, M. Beller, Chem. Eur. J. 2013, 19, 4997.
105. A. Quintard, T. Constantieux, J. Rodriguez, Angew. Chem. 2013, 125, 13121
106. Angew. Chem. Int. Ed. 2013, 52, 12883.
107. M. H. S. A. Hamid, P. A. Slatford, J. M. J. Williams, Adv. Synth. Catal. 2007, 349, 1555
108. A. J. A. Watson, J. M. J. Williams, Science 2010, 329, 635-636
109. G. E. Dobereiner, R. H. Crabtree, Chem. Rev. 2010, 110, 681-703
110. C. Gunanathan, D. Milstein, Science 2013, 341, 1229712.